(Phen­yl)(1-phenyl­sulfonyl-1H-indol-3-yl)methanone

Chakkaravarthi, G.; Panchatcharam, R.; Dhayalan, V.; Mohanakrishnan, A.K.; Manivannan, V.

doi:10.1107/S1600536810042261

organic compounds

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Volume 66| Part 11| November 2010| Page o2895

https://doi.org/10.1107/S1600536810042261

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(Phenyl)(1-phenylsulfonyl-1H-indol-3-yl)methanone

G. Chakkaravarthi,^a ^* R. Panchatcharam,^b V. Dhayalan,^c A. K. Mohanakrishnan ^c and V. Manivannan ^b

^aDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India, ^bDepartment of Research and Development, PRIST University, Vallam, Thanjavur 613 403, Tamil Nadu, India, and ^cDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
^*Correspondence e-mail: chakkaravarthi_2005@yahoo.com

(Received 15 October 2010; accepted 18 October 2010; online 23 October 2010)

In the title compound, C₂₁H₁₅NO₃S, the sulfonyl-bound phenyl ring forms a dihedral angle of 86.28 (5)° with the indole ring system. The molecular structure is stabilized by intramolecular C—H⋯O hydrogen bonds. The crystal packing is stabilized by weak intermolecular C—H⋯O and C—H⋯π interactions.

Related literature

For the structures of closely related compounds, see: Chakkaravarthi et al. (2007 , 2008 ).

Experimental

Crystal data

C₂₁H₁₅NO₃S
M_r = 361.40
Triclinic, $[P \overline 1]$
a = 7.567 (1) Å
b = 10.571 (2) Å
c = 12.083 (3) Å
α = 66.302 (2)°
β = 80.740 (1)°
γ = 78.403 (1)°
V = 863.5 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 295 K
0.24 × 0.22 × 0.20 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.952, T_max = 0.960
15638 measured reflections
4276 independent reflections
3187 reflections with I > 2σ(I)
R_int = 0.026
Standard reflections: 0

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.109
S = 1.01
4276 reflections
235 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C16–C21 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O1	0.93	2.42	2.999 (2)	120
C6—H6⋯O2ⁱ	0.93	2.58	3.493 (2)	167
C7—H7⋯O2ⁱ	0.93	2.54	3.429 (2)	160
C4—H4⋯Cg1ⁱⁱ	0.93	2.98	3.774 (3)	144
Symmetry codes: (i) -x+2, -y, -z; (ii) -x+1, -y, -z.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810042261/bt5379sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810042261/bt5379Isup2.hkl

checkCIF report

Comment top

The geometric parameters of the molecule of (I) (Fig. 1) agree well with the reported values of similar structures (Chakkaravarthi et al., 2007; Chakkaravarthi et al., 2008). The phenyl rings C1—C6 and C16—C21 form the dihedral angles of 86.28 (5)° and 51.91 (5)°, respectively with the indole ring system. The mean planes of the two phenyl rings are inclined at an angle of 42.16 (6)°.

The sum of the bond angles around N1 [358.53°] indicates that N1 atom is sp² hybridized. The molecular structure is stabilized by intra molecular C—H···O hydrogen bonds and the crystal packing is stabilized by weak intermolecular C—H···O and C—H···π [C4—H4···Cg1 (1 - x, -y, -z) distance of 3.774 (3)Å (Cg1 is the centroid of the ring defined by the atoms C16—C21)] interactions.

Related literature top

For the structures of closely related compounds, see: Chakkaravarthi et al. (2007, 2008).

Experimental top

To a solution of 1-phenylsulfonyl-(1H-indol-3-yl)(phenyl)methanol (1 g, 2.75 mmol) in dry 1,2-Dichloroethane (30 ml), manganese dioxide (6 g. 68.96 mmol) was added then stirred at room temperature for 4 h and then refluxed for 3 h. Then the resulting solution was passed through celite pad and washed with DCM (2 x 30 ml). Removal of solvent followed by crystallization from methanol afforded the compound as a colourless crystal.

Structure description top

For the structures of closely related compounds, see: Chakkaravarthi et al. (2007, 2008).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids.
	Fig. 2. The packing of (I), viewed down the a axis. H-bonds are shown as dashed lines; H atoms not involved in hydrogen bonding have been omitted.

(Phenyl)(1-phenylsulfonyl-1H-indol-3-yl)methanone top

Crystal data top

C₂₁H₁₅NO₃S	Z = 2
M_r = 361.40	F(000) = 376
Triclinic, P1	D_x = 1.390 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.567 (1) Å	Cell parameters from 6196 reflections
b = 10.571 (2) Å	θ = 2.2–27.1°
c = 12.083 (3) Å	µ = 0.21 mm⁻¹
α = 66.302 (2)°	T = 295 K
β = 80.740 (1)°	Block, colourless
γ = 78.403 (1)°	0.24 × 0.22 × 0.20 mm
V = 863.5 (3) Å³

Data collection top

Bruker Kappa APEXII diffractometer	4276 independent reflections
Radiation source: fine-focus sealed tube	3187 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ω and φ scans	θ_max = 28.3°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.952, T_max = 0.960	k = −14→13
15638 measured reflections	l = −16→16

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.109	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0543P)² + 0.1447P] where P = (F_o² + 2F_c²)/3
4276 reflections	(Δ/σ)_max < 0.001
235 parameters	Δρ_max = 0.21 e Å⁻³
2 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₂₁H₁₅NO₃S	γ = 78.403 (1)°
M_r = 361.40	V = 863.5 (3) Å³
Triclinic, P1	Z = 2
a = 7.567 (1) Å	Mo Kα radiation
b = 10.571 (2) Å	µ = 0.21 mm⁻¹
c = 12.083 (3) Å	T = 295 K
α = 66.302 (2)°	0.24 × 0.22 × 0.20 mm
β = 80.740 (1)°

Data collection top

Bruker Kappa APEXII diffractometer	4276 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3187 reflections with I > 2σ(I)
T_min = 0.952, T_max = 0.960	R_int = 0.026
15638 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	2 restraints
wR(F²) = 0.109	H-atom parameters constrained
S = 1.01	Δρ_max = 0.21 e Å⁻³
4276 reflections	Δρ_min = −0.29 e Å⁻³
235 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.7233 (2)	0.05722 (16)	0.20701 (13)	0.0494 (4)
C2	0.6154 (3)	0.0869 (2)	0.29978 (15)	0.0648 (5)
H2	0.6523	0.1388	0.3360	0.078*
C3	0.4508 (3)	0.0376 (2)	0.33759 (18)	0.0791 (5)
H3	0.3759	0.0567	0.3997	0.095*
C4	0.3975 (3)	−0.0394 (2)	0.2838 (2)	0.0806 (6)
H4	0.2866	−0.0718	0.3097	0.097*
C5	0.5061 (3)	−0.0687 (2)	0.1928 (2)	0.0757 (5)
H5	0.4690	−0.1215	0.1575	0.091*
C6	0.6701 (2)	−0.02074 (19)	0.15289 (17)	0.0615 (4)
H6	0.7440	−0.0403	0.0906	0.074*
C14	0.80636 (19)	0.40437 (16)	0.04797 (13)	0.0448 (3)
C13	0.7914 (2)	0.44779 (18)	0.14366 (15)	0.0547 (4)
H13	0.8305	0.3873	0.2188	0.066*
C12	0.7164 (2)	0.5838 (2)	0.12251 (18)	0.0641 (5)
H12	0.7018	0.6157	0.1853	0.077*
C11	0.6617 (3)	0.6751 (2)	0.00966 (19)	0.0681 (5)
H11	0.6130	0.7671	−0.0019	0.082*
C10	0.6778 (2)	0.63262 (18)	−0.08489 (17)	0.0609 (4)
H10	0.6412	0.6948	−0.1603	0.073*
C9	0.75050 (19)	0.49375 (16)	−0.06607 (14)	0.0472 (3)
C8	0.7882 (2)	0.41551 (16)	−0.14359 (13)	0.0474 (3)
C7	0.86292 (19)	0.28383 (16)	−0.07641 (12)	0.0469 (3)
H7	0.8982	0.2113	−0.1040	0.056*
C15	0.7413 (2)	0.46868 (18)	−0.26928 (14)	0.0546 (4)
C16	0.8200 (2)	0.39033 (18)	−0.34881 (13)	0.0553 (4)
C21	0.9990 (3)	0.32957 (19)	−0.35204 (14)	0.0634 (5)
H21	1.0737	0.3291	−0.2978	0.076*
C20	1.0679 (3)	0.2692 (2)	−0.43577 (17)	0.0807 (6)
H20	1.1893	0.2301	−0.4391	0.097*
C19	0.9549 (4)	0.2676 (2)	−0.51451 (18)	0.0891 (6)
H19	1.0000	0.2259	−0.5700	0.107*
C18	0.7771 (4)	0.3274 (3)	−0.51087 (19)	0.0900 (6)
H18	0.7017	0.3266	−0.5642	0.108*
C17	0.7103 (3)	0.3879 (2)	−0.42929 (16)	0.0742 (5)
H17	0.5894	0.4283	−0.4275	0.089*
N1	0.87874 (17)	0.27365 (13)	0.04012 (10)	0.0461 (3)
O1	0.98538 (16)	0.15404 (13)	0.24616 (10)	0.0602 (3)
O2	1.04747 (14)	0.03484 (12)	0.10209 (10)	0.0543 (3)
O3	0.63449 (19)	0.57703 (15)	−0.30880 (11)	0.0789 (4)
S1	0.92933 (5)	0.12195 (4)	0.15505 (3)	0.04628 (13)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0554 (8)	0.0428 (8)	0.0381 (7)	0.0021 (7)	−0.0076 (6)	−0.0064 (6)
C2	0.0723 (11)	0.0626 (11)	0.0470 (9)	−0.0010 (9)	0.0007 (8)	−0.0146 (8)
C3	0.0696 (12)	0.0795 (14)	0.0578 (11)	0.0037 (10)	0.0110 (9)	−0.0082 (9)
C4	0.0579 (10)	0.0687 (13)	0.0827 (14)	−0.0089 (9)	−0.0036 (10)	0.0032 (9)
C5	0.0669 (11)	0.0698 (13)	0.0848 (14)	−0.0156 (10)	−0.0104 (10)	−0.0201 (11)
C6	0.0619 (10)	0.0604 (11)	0.0593 (10)	−0.0069 (8)	−0.0060 (8)	−0.0209 (8)
C14	0.0447 (7)	0.0433 (8)	0.0444 (7)	−0.0093 (6)	−0.0023 (6)	−0.0140 (6)
C13	0.0606 (9)	0.0553 (10)	0.0513 (9)	−0.0105 (8)	−0.0034 (7)	−0.0234 (8)
C12	0.0666 (10)	0.0632 (12)	0.0739 (12)	−0.0113 (9)	−0.0011 (9)	−0.0391 (10)
C11	0.0712 (11)	0.0486 (10)	0.0844 (13)	−0.0044 (8)	−0.0049 (10)	−0.0280 (10)
C10	0.0611 (10)	0.0473 (9)	0.0632 (10)	−0.0049 (8)	−0.0074 (8)	−0.0107 (8)
C9	0.0440 (7)	0.0465 (8)	0.0456 (8)	−0.0096 (6)	−0.0016 (6)	−0.0115 (6)
C8	0.0483 (8)	0.0496 (9)	0.0386 (7)	−0.0083 (6)	−0.0041 (6)	−0.0105 (6)
C7	0.0535 (8)	0.0499 (9)	0.0359 (7)	−0.0072 (7)	−0.0052 (6)	−0.0149 (6)
C15	0.0546 (8)	0.0571 (10)	0.0403 (8)	−0.0080 (7)	−0.0082 (7)	−0.0053 (7)
C16	0.0677 (10)	0.0550 (10)	0.0337 (7)	−0.0120 (8)	−0.0094 (7)	−0.0041 (7)
C21	0.0728 (11)	0.0691 (12)	0.0399 (8)	−0.0044 (9)	−0.0087 (8)	−0.0138 (8)
C20	0.1019 (15)	0.0786 (14)	0.0471 (10)	0.0032 (12)	0.0000 (10)	−0.0194 (9)
C19	0.1479 (17)	0.0736 (14)	0.0441 (9)	−0.0172 (13)	−0.0036 (12)	−0.0223 (10)
C18	0.1306 (15)	0.0951 (17)	0.0512 (10)	−0.0334 (13)	−0.0220 (12)	−0.0222 (11)
C17	0.0873 (13)	0.0821 (14)	0.0465 (9)	−0.0182 (11)	−0.0203 (9)	−0.0097 (9)
N1	0.0566 (7)	0.0434 (7)	0.0357 (6)	−0.0037 (6)	−0.0071 (5)	−0.0132 (5)
O1	0.0728 (7)	0.0643 (7)	0.0457 (6)	−0.0020 (6)	−0.0197 (5)	−0.0220 (5)
O2	0.0551 (6)	0.0540 (7)	0.0498 (6)	0.0039 (5)	−0.0072 (5)	−0.0205 (5)
O3	0.0817 (9)	0.0791 (9)	0.0539 (7)	0.0174 (7)	−0.0184 (6)	−0.0119 (7)
S1	0.0526 (2)	0.0470 (2)	0.03579 (19)	0.00011 (16)	−0.00991 (15)	−0.01356 (15)

Geometric parameters (Å, º) top

C1—C2	1.381 (2)	C10—H10	0.9300
C1—C6	1.386 (2)	C9—C8	1.444 (2)
C1—S1	1.7498 (17)	C8—C7	1.356 (2)
C2—C3	1.384 (3)	C8—C15	1.468 (2)
C2—H2	0.9300	C7—N1	1.3913 (18)
C3—C4	1.375 (3)	C7—H7	0.9300
C3—H3	0.9300	C15—O3	1.227 (2)
C4—C5	1.364 (3)	C15—C16	1.490 (2)
C4—H4	0.9300	C16—C21	1.379 (2)
C5—C6	1.376 (3)	C16—C17	1.387 (2)
C5—H5	0.9300	C21—C20	1.385 (3)
C6—H6	0.9300	C21—H21	0.9300
C14—C13	1.387 (2)	C20—C19	1.385 (3)
C14—C9	1.397 (2)	C20—H20	0.9300
C14—N1	1.4152 (19)	C19—C18	1.369 (3)
C13—C12	1.370 (2)	C19—H19	0.9300
C13—H13	0.9300	C18—C17	1.361 (3)
C12—C11	1.388 (3)	C18—H18	0.9300
C12—H12	0.9300	C17—H17	0.9300
C11—C10	1.366 (3)	N1—S1	1.6677 (12)
C11—H11	0.9300	O1—S1	1.4195 (11)
C10—C9	1.399 (2)	O2—S1	1.4195 (11)

C2—C1—C6	121.26 (17)	C7—C8—C9	107.38 (13)
C2—C1—S1	119.33 (14)	C7—C8—C15	127.21 (15)
C6—C1—S1	119.39 (12)	C9—C8—C15	125.29 (15)
C1—C2—C3	118.46 (19)	C8—C7—N1	109.68 (13)
C1—C2—H2	120.8	C8—C7—H7	125.2
C3—C2—H2	120.8	N1—C7—H7	125.2
C4—C3—C2	120.39 (18)	O3—C15—C8	119.99 (16)
C4—C3—H3	119.8	O3—C15—C16	119.61 (14)
C2—C3—H3	119.8	C8—C15—C16	120.39 (14)
C5—C4—C3	120.5 (2)	C21—C16—C17	118.93 (18)
C5—C4—H4	119.7	C21—C16—C15	123.05 (15)
C3—C4—H4	119.7	C17—C16—C15	117.84 (17)
C4—C5—C6	120.5 (2)	C16—C21—C20	120.24 (18)
C4—C5—H5	119.8	C16—C21—H21	119.9
C6—C5—H5	119.8	C20—C21—H21	119.9
C5—C6—C1	118.91 (18)	C21—C20—C19	119.5 (2)
C5—C6—H6	120.5	C21—C20—H20	120.2
C1—C6—H6	120.5	C19—C20—H20	120.2
C13—C14—C9	122.50 (15)	C18—C19—C20	120.2 (2)
C13—C14—N1	130.70 (14)	C18—C19—H19	119.9
C9—C14—N1	106.78 (13)	C20—C19—H19	119.9
C12—C13—C14	117.03 (16)	C17—C18—C19	120.1 (2)
C12—C13—H13	121.5	C17—C18—H18	120.0
C14—C13—H13	121.5	C19—C18—H18	120.0
C13—C12—C11	121.58 (17)	C18—C17—C16	121.0 (2)
C13—C12—H12	119.2	C18—C17—H17	119.5
C11—C12—H12	119.2	C16—C17—H17	119.5
C10—C11—C12	121.37 (17)	C7—N1—C14	108.35 (12)
C10—C11—H11	119.3	C7—N1—S1	123.27 (10)
C12—C11—H11	119.3	C14—N1—S1	126.91 (10)
C11—C10—C9	118.68 (17)	O2—S1—O1	120.91 (7)
C11—C10—H10	120.7	O2—S1—N1	105.43 (7)
C9—C10—H10	120.7	O1—S1—N1	106.66 (7)
C14—C9—C10	118.82 (15)	O2—S1—C1	108.92 (7)
C14—C9—C8	107.78 (14)	O1—S1—C1	109.22 (7)
C10—C9—C8	133.37 (15)	N1—S1—C1	104.41 (7)

C6—C1—C2—C3	−0.4 (3)	C8—C15—C16—C21	−42.0 (2)
S1—C1—C2—C3	178.44 (13)	O3—C15—C16—C17	−35.9 (2)
C1—C2—C3—C4	0.2 (3)	C8—C15—C16—C17	142.89 (16)
C2—C3—C4—C5	0.2 (3)	C17—C16—C21—C20	1.0 (3)
C3—C4—C5—C6	−0.5 (3)	C15—C16—C21—C20	−174.08 (16)
C4—C5—C6—C1	0.3 (3)	C16—C21—C20—C19	−1.4 (3)
C2—C1—C6—C5	0.2 (3)	C21—C20—C19—C18	1.1 (3)
S1—C1—C6—C5	−178.69 (14)	C20—C19—C18—C17	−0.4 (4)
C9—C14—C13—C12	0.7 (2)	C19—C18—C17—C16	0.0 (3)
N1—C14—C13—C12	178.95 (15)	C21—C16—C17—C18	−0.3 (3)
C14—C13—C12—C11	−1.5 (3)	C15—C16—C17—C18	175.06 (18)
C13—C12—C11—C10	1.0 (3)	C8—C7—N1—C14	1.51 (16)
C12—C11—C10—C9	0.3 (3)	C8—C7—N1—S1	168.55 (10)
C13—C14—C9—C10	0.5 (2)	C13—C14—N1—C7	−179.63 (15)
N1—C14—C9—C10	−178.11 (13)	C9—C14—N1—C7	−1.22 (16)
C13—C14—C9—C8	179.08 (14)	C13—C14—N1—S1	13.9 (2)
N1—C14—C9—C8	0.51 (16)	C9—C14—N1—S1	−167.65 (10)
C11—C10—C9—C14	−1.0 (2)	C7—N1—S1—O2	33.46 (13)
C11—C10—C9—C8	−179.16 (16)	C14—N1—S1—O2	−161.98 (12)
C14—C9—C8—C7	0.40 (16)	C7—N1—S1—O1	163.18 (12)
C10—C9—C8—C7	178.74 (17)	C14—N1—S1—O1	−32.27 (14)
C14—C9—C8—C15	176.58 (14)	C7—N1—S1—C1	−81.25 (13)
C10—C9—C8—C15	−5.1 (3)	C14—N1—S1—C1	83.30 (13)
C9—C8—C7—N1	−1.18 (17)	C2—C1—S1—O2	155.20 (12)
C15—C8—C7—N1	−177.26 (14)	C6—C1—S1—O2	−25.92 (15)
C7—C8—C15—O3	161.36 (17)	C2—C1—S1—O1	21.21 (15)
C9—C8—C15—O3	−14.1 (2)	C6—C1—S1—O1	−159.91 (13)
C7—C8—C15—C16	−17.5 (2)	C2—C1—S1—N1	−92.56 (13)
C9—C8—C15—C16	167.13 (14)	C6—C1—S1—N1	86.32 (14)
O3—C15—C16—C21	139.19 (18)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C16–C21 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1	0.93	2.59	2.934 (2)	103
C10—H10···O3	0.93	2.57	3.068 (3)	114
C13—H13···O1	0.93	2.42	2.999 (2)	120
C6—H6···O2ⁱ	0.93	2.58	3.493 (2)	167
C7—H7···O2ⁱ	0.93	2.54	3.429 (2)	160
C4—H4···Cg1ⁱⁱ	0.93	2.98	3.774 (3)	144

Symmetry codes: (i) −x+2, −y, −z; (ii) −x+1, −y, −z.

Experimental details

Crystal data
Chemical formula	C₂₁H₁₅NO₃S
M_r	361.40
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	7.567 (1), 10.571 (2), 12.083 (3)
α, β, γ (°)	66.302 (2), 80.740 (1), 78.403 (1)
V (Å³)	863.5 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.24 × 0.22 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.952, 0.960
No. of measured, independent and observed [I > 2σ(I)] reflections	15638, 4276, 3187
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.109, 1.01
No. of reflections	4276
No. of parameters	235
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.29

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C16–C21 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1	0.93	2.59	2.934 (2)	103
C10—H10···O3	0.93	2.57	3.068 (3)	114
C13—H13···O1	0.93	2.42	2.999 (2)	120
C6—H6···O2ⁱ	0.93	2.58	3.493 (2)	167
C7—H7···O2ⁱ	0.93	2.54	3.429 (2)	160
C4—H4···Cg1ⁱⁱ	0.93	2.98	3.774 (3)	144

Symmetry codes: (i) −x+2, −y, −z; (ii) −x+1, −y, −z.

Acknowledgements

The authors wish to acknowledge DV University of Madras for the data collection.

References

Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chakkaravarthi, G., Dhayalan, V., Mohanakrishnan, A. K. & Manivannan, V. (2007). Acta Cryst. E63, o3698. Web of Science CSD CrossRef IUCr Journals Google Scholar
Chakkaravarthi, G., Dhayalan, V., Mohanakrishnan, A. K. & Manivannan, V. (2008). Acta Cryst. E64, o542. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS, University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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